CN107814718A - A kind of synthetic method of 2,2,4 TMPD monoesters - Google Patents
A kind of synthetic method of 2,2,4 TMPD monoesters Download PDFInfo
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- CN107814718A CN107814718A CN201711125582.6A CN201711125582A CN107814718A CN 107814718 A CN107814718 A CN 107814718A CN 201711125582 A CN201711125582 A CN 201711125582A CN 107814718 A CN107814718 A CN 107814718A
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- molecular sieve
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
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Abstract
The present invention relates to a kind of synthetic method of 2,2,4 TMPD monoesters, the synthetic method comprises the following steps:In the presence of acidic, alkyl aldehyde compound carries out condensation reaction 15 hours;Obtained mixture passes through separating-purifying, obtains 2,2,4 TMPD monoesters;The acidic catalyst is the mixture of oxalic acid and molecular sieve, and the molecular sieve zeolites molecular sieve, the zeolite molecular sieve surface has Bronsted acid position;The present invention is greatly suppressed by using specific catalyst, dehydration so that the selectivity of reaction greatly improves.
Description
Technical field
The present invention relates to a kind of synthetic method of 2,2,4- TMPDs monoesters.
Background technology
The building in China and adnornment industry fast development, therefore requirement of the people to quality of life improves constantly and with ring
The continuous enhancing of consciousness is protected, control of the coating industry to VOC (boiling point is less than 250 DEG C of VOC) content enters one
Step is strict, and the water emulsion coating as one of ornament materials has turned into the material of main part of inner wall of building decoration, while builds outer
Wall decorative applications rate is also up to 35%.The many emulsion polymers used in emulsion paint at normal temperatures can not film forming, because big absolutely under low temperature
Most emulsion polymers are all unable to film forming.To make emulsion paint form complete film, it is necessary to which the film forming that addition can play coalescence effect helps
Agent.Coalescents are typically that dissolubility is very strong and the slowly solvent of volatilization, such as alcohol ester (Lauryl Alcohol ester) class, glycol ether
Class and ethylene glycol esters, they can soften emulsion polymerization composition granule, be merged the coalescence of these particles, preferably formed
Film.Coalescents except emulsion paint MFT (MFT) is reduced, can also improve the weatherability of emulsion paint, washable property,
The paint film properties such as the color developing of coating.
2,2,4- TMPD monoesters are emerging green additives, and application is more and more extensive, are helped with common film forming
Agent is compared, and 2,2,4- TMPD monoesters have many advantages, such as:Resin intermiscibility is good, and dosage is few, and film-forming temperature is low, film levelling
Property, color developing are good, and freezing point is low, and hydrolytic stability is good, and toxicity is low, is a kind of fabulous emulsion paint coalescents, can be effective
Ground is used in polyvinyl acetate homopolymer, copolymer and trimer, and pure acrylic acid, styrene/acrylic, poly- butylbenzene ethene
In the latex such as ethylene vinyl acetate.
In existing synthetic method, due to reacting in acid condition, dehydration easily occurs for synthesis material so for preparing
Contain substantial amounts of double bond in obtained mixture, the selectivity of synthetic reaction is low.
The content of the invention
In order to solve the above-mentioned technical problem, the invention provides a kind of synthesis side of 2,2,4- TMPD monoesters
Method, the synthetic method comprise the following steps:
In the presence of acidic, alkyl aldehyde compound carries out condensation reaction 1-5 hours;
Obtained mixture passes through separating-purifying, obtains 2,2,4- TMPD monoesters;
The acidic catalyst is the mixture of oxalic acid and molecular sieve, the molecular sieve zeolites molecular sieve, the zeolite molecular sieve
Surface has Bronsted acid position;
The structure of the alkyl aldehyde compound is as follows:
The R1、R2For methyl.
As a kind of perferred technical scheme, the mass ratio of the oxalic acid and acidic molecular sieve is 1:10-50.
As a kind of perferred technical scheme, the reaction temperature of the condensation reaction is 50-120 degrees Celsius.
As a kind of perferred technical scheme, the condensation reaction includes first stage and second stage, first rank
Section is to be reacted under 70-80 degrees Celsius 10-30 minutes, and the second stage is that 10-60 points are reacted under 100-110 degrees Celsius
Clock.
As a kind of perferred technical scheme, SiO2 and Al2O3 mol ratios are 5-25 in the acidic molecular sieve.
The present invention is greatly suppressed by using specific catalyst, dehydration so that the selectivity of reaction
Greatly improve.
The above-mentioned of the application and other features, aspect and advantage is more readily understood with reference to described further below.
Embodiment
Unless otherwise defined, all technologies used herein and scientific terminology have and the common skill of art of the present invention
The identical implication that art personnel are generally understood that.When contradiction be present, the definition in this specification is defined.
The synthetic method of one kind 2,2,4- TMPD monoesters, the synthetic method comprise the following steps:
In the presence of acidic, alkyl aldehyde compound carries out condensation reaction 1-5 hours;
Obtained mixture passes through separating-purifying, obtains 2,2,4- TMPD monoesters;
The acidic catalyst is the mixture of oxalic acid and molecular sieve, the molecular sieve zeolites molecular sieve, the zeolite molecular sieve
Surface has Bronsted acid position;
The structure of the alkyl aldehyde compound is as follows:
The structure of the 2,2,4- TMPDs monoesters is as follows:
The R1、R2For methyl.
The molecular sieve of the present invention is the porous plastid for having the uniform pore of fine pore.Wherein, molecular sieve zeolites and molecule
The form of sieve activated carbon is not particularly limited, such as can be granular or graininess.
The molecular sieve surface of the present invention has acidity, and there are 4 aspects in the acid source of molecular sieve surface:
(1), the OH bases on molecular sieve surface show sour position center;(2), the outer aluminium ion meeting intensified acid position of skeleton, forms L acid sites;
(3), polyvalent cation may also produce OH bases and show sour position center;(4), transition metal ions reduction can also form sour position center.
For example, the NaY types molecular sieve of synthesis carries out ion exchange, NaY+NH4Cl → NH4Y+NaCl in NH4Cl solution
Heating deamination becomes HY molecular sieves NH4Y → HY+NH3, one is left with aluminum-oxygen tetrahedron in skeleton after ammonia effusion
Bronsted acid, there is the molecular sieve of Bronsted acid so as to which surface be prepared.
The preparation method of acidic molecular sieve with L acid sites:The aluminium ion of three-fold coordination is easily from molecule in framework of molecular sieve
Deviate from sieve skeleton frame, be present in (AlO)+or (AlO) p+ cationic forms in hole, turn into L acid sites;When (AlO) p+ sun
When ion interacts with OH base acid positions center, L acid position center can be made to be strengthened.The L acid that the outer aluminium ion of molecular skeleton is formed
Center:The aluminium ion of three-fold coordination is easily deviate from from framework of molecular sieve in framework of molecular sieve, with (AlO)+or (AlO) p+ cation shapes
Formula is present in hole, turns into L acid sites;When (AlO) p+ cations and OH base acid positions center interact, L acid position can be made
Strengthened at center.
Preparation method with the centrical acidic molecular sieve of OH bases acid:Na+ is by multivalent metal cation(As Ca2+, Mg2
+, La3+ etc.)After exchange, absorption water or the crystallization water in molecular sieve can form hydrated ion with polyvalent cation.Through drying dehydration
To a certain extent, multivalent metal cation gradually strengthens the polarization of hydrone, and last H2O is thermally treated to dissociate H+,
Generate OH acid sites.
The preparation method of acidic molecular sieve with transition metal ions:In the presence of transition metal tufted thing, facing hydrogen bar
Under part, molecule H2 and proton can be promoted(H+)Between mutual conversion.
Ion-exchange degree:Refer to the percentage that the sodium ion exchanged accounts for original sodium ion in zeolite molecular sieve.The present invention
The exchange degree of acidic molecular sieve can select the acidic molecular sieves of 30%-99% exchange degrees.
Zeolite refers to the aluminosilicate shown in following formulas as a kind of common molecular sieve, zeolite of the invention,
Chemical formula is as follows:
xM2/nO·Al2O3·ySiO2·zH2O
Herein,
M be cation (for example, the alkaline-earth metal of Li+, Na+, K+ etc. alkali metal ion and/or Mg2+, Ca2+, Ba2+ etc. from
Son etc.),
N is cation M valence mumber,
X is less than 1 number (for example, 0.01 to 1),
Y is more than 2 number (for example, 2 to 100),
Z is the number (for example, 0 to 10) more than 0.
The cation of alkali metal and/or alkaline-earth metal etc. and/or hydrone etc. can be maintained in pore by zeolite.But
Optionally, by after the cation replacement of the alkali metal in pore and/or alkaline-earth metal etc., acidic molecular sieve has been obtained.It is general and
Speech, hydrone in the pore of zeolite etc. is heated and after removing, zeolite is this area skill as the zeolite user activated
Thing known to art personnel.The removal of cation and/or hydrone of alkali metal and/or alkaline-earth metal in pore etc. etc.
Degree and method, it can be properly selected and be adjusted by those skilled in the art.For example, by heating, or heat and depressurize and go
The degree and method for removing water molecule can be properly selected and adjusted by those skilled in the art.The present invention also can be used directly commercially available
Activation zeolite.
The oxalic acid of the present invention and the mass ratio of acidic molecular sieve are 1:10-50.
The reaction temperature of the condensation reaction of the present invention is 50-120 degrees Celsius.
The condensation reaction of the present invention includes first stage and second stage, and the first stage is under 70-80 degrees Celsius
React 10-30 minutes, the second stage is that 10-60 minutes are reacted under 100-110 degrees Celsius.
SiO2 and Al2O3 mol ratios are 5-25 in the acidic molecular sieve of the present invention.
Hereinafter, the present invention is explained in more detail by embodiment, it should be appreciated that these embodiments are only
It is illustrating and nonrestrictive.If without other explanations, raw materials used is all commercially available.
The present invention is described in detail referring to several examples.
HY type zeolite 2,2,4- TMPD monoesters SiO2/Al2O3 mol ratios 18;
HY type zeolite 2,2,4- TMPD monoesters SiO2/Al2O3 mol ratios 23.
Embodiment 1
Equipped with condenser, agitating device, thermometer reactor in, add 2g2,2,4- TMPD monoesters HY types boiling
Stone(H-ZSM-52,2,4- TMPD monoesters, exchange degree 90%, SiO2/Al2O3 mol ratios 18)And 0.05g oxalic acid,
The isobutylaldehyde for adding 200g carries out condensation reaction, and controlling reaction temperature reacts 25 at 70-80 degrees Celsius under 70-80 degrees Celsius
Minute, 100 degrees Celsius are warming up to, the controlling reaction temperature reacts 50 at 100-110 degrees Celsius under 100-110 degrees Celsius
Minute, Synthesis liquid is prepared.It is evaporated under reduced pressure under the conditions of pressure is -0.097MPa, obtains 2,2,4- trimethyls -1,3-
Pentanediol mono isobutyrate.Synthesis liquid is analyzed, the conversion ratio of isobutylaldehyde is 86.9%, 2,2,4- trimethyl -1,3- pentanediol Dan Yi
Butyrate is selectively 96.9%.
Embodiment 2
Equipped with condenser, agitating device, thermometer reactor in, add 2g2,2,4- TMPD monoesters HY types boiling
Stone(H-ZSM-52,2,4- TMPD monoesters, exchange degree 90%, SiO2/Al2O3 mol ratios 23)And 0.1g oxalic acid, add
The isobutylaldehyde for entering 200g carries out condensation reaction, and controlling reaction temperature reacts 25 points at 70-80 degrees Celsius under 70-80 degrees Celsius
Clock, 100 degrees Celsius are warming up to, the controlling reaction temperature reacts 40 points at 100-110 degrees Celsius under 100-110 degrees Celsius
Clock, Synthesis liquid is prepared.It is evaporated under reduced pressure under the conditions of pressure is -0.097MPa, obtains 2,2,4- trimethyls -1,3- penta
Monoisobutyrate.Synthesis liquid is analyzed, the conversion ratio of isobutylaldehyde is 88.3%, 2,2,4- trimethyl -1,3- pentanediol list isobutyls
Acid esters is selectively 96.2%.
Embodiment 3
Equipped with condenser, agitating device, thermometer reactor in, add 2g2,2,4- TMPD monoesters HY types boiling
Stone(H-ZSM-52,2,4- TMPD monoesters, exchange degree 90%, SiO2/Al2O3 mol ratios 10)And 0.15g oxalic acid,
The isobutylaldehyde for adding 200g carries out condensation reaction, and controlling reaction temperature reacts 15 at 70-80 degrees Celsius under 70-80 degrees Celsius
Minute, 100 degrees Celsius are warming up to, the controlling reaction temperature reacts 50 at 100-110 degrees Celsius under 100-110 degrees Celsius
Minute, Synthesis liquid is prepared.It is evaporated under reduced pressure under the conditions of pressure is -0.097MPa, obtains 2,2,4- trimethyls -1,3-
Pentanediol mono isobutyrate.Synthesis liquid is analyzed, the conversion ratio of isobutylaldehyde is 86.9%, 2,2,4- trimethyl -1,3- pentanediol Dan Yi
Butyrate is selectively 96.9%.
Comparative example 1
Equipped with condenser, agitating device, thermometer reactor in, add 2g2,2,4- TMPD monoesters HY types boiling
Stone(H-ZSM-52,2,4- TMPD monoesters, exchange degree 90%, SiO2/Al2O3 mol ratios 18), add 200g isobutyl
Aldehyde carries out condensation reaction, and controlling reaction temperature is reacted 25 minutes under 70-80 degrees Celsius at 70-80 degrees Celsius, is warming up to 100
Degree Celsius, the controlling reaction temperature is reacted 50 minutes under 100-110 degrees Celsius at 100-110 degrees Celsius, conjunction is prepared
Into liquid.It is evaporated under reduced pressure under the conditions of pressure is -0.097MPa, obtains 2,2,4- trimethyl -1,3- pentanediol list isobutyric acids
Ester.Synthesis liquid is analyzed, the conversion ratio of isobutylaldehyde is 87.9%, and 2,2,4- trimethyl -1,3- pentanediol mono isobutyrates are selectively
67.4%。
Comparative example 2
Equipped with condenser, agitating device, thermometer reactor in, add 2g oxalic acid, the isobutylaldehyde for adding 200g contracted
Reaction is closed, controlling reaction temperature is reacted 25 minutes under 70-80 degrees Celsius at 70-80 degrees Celsius, is warming up to 100 degrees Celsius, institute
Controlling reaction temperature is stated at 100-110 degrees Celsius, is reacted 50 minutes under 100-110 degrees Celsius, Synthesis liquid is prepared.Pressing
Power is evaporated under reduced pressure under the conditions of being -0.097MPa, obtains 2,2,4- trimethyl -1,3- pentanediol mono isobutyrates.Analysis is closed
Into liquid, the conversion ratio of isobutylaldehyde is 65.2%, and 2,2,4- trimethyl -1,3- pentanediol mono isobutyrates are selectively 75.8%.
Comparative example 3
Equipped with condenser, agitating device, thermometer reactor in, add 2g2,2,4- TMPD monoesters HY types boiling
Stone(H-ZSM-52,2,4- TMPD monoesters, exchange degree 90%, SiO2/Al2O3 mol ratios 18)And 2g oxalic acid, add
200g isobutylaldehyde carries out condensation reaction, and controlling reaction temperature is reacted 25 minutes at 70-80 degrees Celsius under 70-80 degrees Celsius,
100 degrees Celsius are warming up to, the controlling reaction temperature is reacted 50 minutes at 100-110 degrees Celsius under 100-110 degrees Celsius,
Synthesis liquid is prepared.It is evaporated under reduced pressure under the conditions of pressure is -0.097MPa, obtains 2,2,4- trimethyls -1,3- penta 2
Alcohol mono isobutyrate.Synthesis liquid is analyzed, the conversion ratio of isobutylaldehyde is 71.1%, 2,2,4- trimethyl -1,3- pentanediol list isobutyric acids
Ester is selectively 91.4%.
Comparative example 4
Equipped with condenser, agitating device, thermometer reactor in, add 2g2,2,4- TMPD monoesters HY types boiling
Stone(H-ZSM-52,2,4- TMPD monoesters, exchange degree 90%, SiO2/Al2O3 mol ratios 30)And 0.05g oxalic acid,
The isobutylaldehyde for adding 200g carries out condensation reaction, and controlling reaction temperature reacts 25 at 70-80 degrees Celsius under 70-80 degrees Celsius
Minute, 100 degrees Celsius are warming up to, the controlling reaction temperature reacts 50 at 100-110 degrees Celsius under 100-110 degrees Celsius
Minute, Synthesis liquid is prepared.It is evaporated under reduced pressure under the conditions of pressure is -0.097MPa, obtains 2,2,4- trimethyls -1,3-
Pentanediol mono isobutyrate.Synthesis liquid is analyzed, the conversion ratio of isobutylaldehyde is 82.9%, 2,2,4- trimethyl -1,3- pentanediol Dan Yi
Butyrate is selectively 91.0%.
The foregoing is only a preferred embodiment of the present invention, is not intended to limit the scope of the present invention.It is every
The equivalent changes and modifications done according to present invention, it is encompassed by the scope of the claims of the present invention.
Claims (5)
1. one kind 2,2, the synthetic method of 4- TMPD monoesters, it is characterised in that the synthetic method includes following step
Suddenly:
In the presence of acidic, alkyl aldehyde compound carries out condensation reaction 1-5 hours;
Obtained mixture passes through separating-purifying, obtains 2,2,4- TMPD monoesters;
The acidic catalyst is the mixture of oxalic acid and molecular sieve, the molecular sieve zeolites molecular sieve, the zeolite molecular sieve
Surface has Bronsted acid position;
The structure of the alkyl aldehyde compound is as follows:
The R1、R2For methyl.
2. according to claim 1 a kind of 2, the synthetic method of 2,4- TMPD monoesters, it is characterised in that described
The mass ratio of oxalic acid and acidic molecular sieve is 1:10-50.
3. according to claim 1 a kind of 2, the synthetic method of 2,4- TMPD monoesters, it is characterised in that described
The reaction temperature of condensation reaction is 50-120 degrees Celsius.
4. according to claim 1 a kind of 2, the synthetic method of 2,4- TMPD monoesters, it is characterised in that described
Condensation reaction includes first stage and second stage, and the first stage is that 10-30 minutes, institute are reacted under 70-80 degrees Celsius
It is that 10-60 minutes are reacted under 100-110 degrees Celsius to state second stage.
5. according to claim 1 a kind of 2, the synthetic method of 2,4- TMPD monoesters, it is characterised in that described
SiO2 and Al2O3 mol ratios are 5-25 in acidic molecular sieve.
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